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$54+ Cheap flights from Pennsylvania to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Pennsylvania to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Pennsylvania (USPA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$108
(Frontier)

One-way from

$54
(Frontier)
From Pennsylvania to Chicago (CHI)
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One-way flight from Pennsylvania to Chicago (CHI)
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Find flight deals from Pennsylvania to Chicago

Cheapest flights from Pennsylvania to Chicago
Explore the most affordable flight options available from Pennsylvania to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:59 pmPHL - ORD
Nonstop2h 28mFrontier
Wed 1/110:22 pmORD - PHL
Nonstop2h 07mFrontier
Deal found 12/17$106
This Gotogate deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/285:35 pmEWR - ORD
Nonstop2h 44mSpirit Airlines
Sat 1/41:24 pmORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/18$139
This Booking.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:59 pmLGA - ORD
1 stop13h 38mMultiple Airlines
Tue 1/73:00 pmORD - LGA
1 stop6h 00mMultiple Airlines
Deal found 12/17$142
This Cheapflightsfares deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:05 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Wed 1/811:12 amORD - LGA
Nonstop2h 12mSpirit Airlines
Deal found 12/17$144
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:43 amPHL - MDW
Nonstop2h 26mFrontier
Wed 1/18:25 amMDW - PHL
1 stop7h 59mFrontier
Deal found 12/17$169
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:59 pmPHL - ORD
Nonstop2h 28mMultiple Airlines
Tue 1/142:02 pmORD - PHL
1 stop7h 14mMultiple Airlines
Deal found 12/16$171
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:30 pmLGA - MDW
Nonstop2h 30mSouthwest
Wed 1/88:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/17$194
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:00 amJFK - ORD
Nonstop2h 46mAmerican Airlines
Wed 1/84:22 pmORD - JFK
Nonstop2h 18mAmerican Airlines
Deal found 12/17$202
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/267:00 amLGA - ORD
1 stop5h 01mAmerican Airlines
Wed 1/811:06 amORD - LGA
Nonstop2h 08mAmerican Airlines
Deal found 12/17$207
This Frontier deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3012:20 pmLGA - MDW
1 stop11h 54mFrontier
Thu 1/97:30 amMDW - LGA
1 stop8h 30mFrontier
Deal found 12/17$208
This Booking.com deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/285:35 pmEWR - ORD
Nonstop2h 44mMultiple Airlines
Sun 1/58:03 pmORD - EWR
1 stop13h 54mMultiple Airlines
Deal found 12/18$220
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:10 pmEWR - ORD
Nonstop2h 42mUnited Airlines
Tue 1/76:00 amORD - EWR
Nonstop2h 11mUnited Airlines
Deal found 12/17$232

Find flights from Pennsylvania to Chicago within your budget

Customize your flight search to find flights from Pennsylvania to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 1/27

6:05 am-3:02 pm

1 stop9h 57m

Chicago Midway

Thu 1/30

7:15 am-8:48 pm

1 stop12h 33m

$108

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 1/9

4:45 pm-10:42 pm

1 stop6h 57m

Chicago O'Hare Intl

Mon 1/13

3:25 pm-2:06 pm

1 stop21h 41m

$116

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 1/27

11:00 am-10:27 pm

1 stop12h 27m

Chicago O'Hare Intl

Thu 1/30

6:36 pm-6:30 am

1 stop10h 54m

$124

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 1/29

11:00 am-7:06 pm

1 stop9h 06m

Chicago Midway

Fri 1/31

3:37 pm-1:59 pm

1 stop21h 22m

$124

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 1/29

5:00 pm-9:27 am

1 stop17h 27m

Chicago O'Hare Intl

Sun 2/2

4:18 pm-10:00 am

1 stop16h 42m

$124

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 1/11

9:15 pm-10:55 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 1/13

8:38 am-3:10 pm

1 stop5h 32m

$125

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 1/16

9:15 pm-10:55 pm

Nonstop2h 40m

Chicago O'Hare Intl

Tue 1/21

7:00 am-10:04 am

Nonstop2h 04m

$126

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Mon 1/13

4:45 pm-10:35 pm

1 stop6h 50m

Chicago O'Hare Intl

Wed 1/15

2:02 pm-10:16 pm

1 stop7h 14m

$126

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/18

5:00 pm-10:02 am

1 stop18h 02m

Chicago Midway

Sun 1/26

10:58 am-9:45 am

1 stop21h 47m

$126

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 1/24

7:59 am-9:34 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 1/27

5:50 am-9:06 am

Nonstop2h 16m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 60 results
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Best time to book a flight from Pennsylvania to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Pennsylvania with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Pennsylvania to Chicago

Get recent, data-driven insights about flights from Pennsylvania to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Pennsylvania to Chicago?

Currently, September is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $232). Flying from Pennsylvania to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PA to CHI?

Find hourly flight availability from Pennsylvania to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago as you normally would.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 18, 2024.
To help decide which airline to fly from Pennsylvania to Chicago, see what other customers have to say about Spirit Airlines, Delta and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Pennsylvania to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Pennsylvania to Chicago one-way?

    $54 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $70 and $73, respectively.

  • What are the most popular routes from Pennsylvania to Chicago?

    When deciding which route to take from Pennsylvania to Chicago consider New York John F Kennedy Intl - Chicago O'Hare Intl, Newark - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Pennsylvania to Chicago?

    No one likes to see their flight delayed. When booking a flight from Pennsylvania to Chicago consider choosing Republic Airways (100%), Japan Airlines (97%) or ANA (91%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Pennsylvania to Chicago?

    On average you can expect to pay $1,031 for a flight from Pennsylvania to Chicago. The cheapest flight overall is $68 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $145.

  • Can I find deals for flights from Pennsylvania to Chicago that include hotel bookings?

    Yes. In addition to deals on Pennsylvania to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pennsylvania to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pennsylvania to Chicago.

  • Can I find deals for business class flights from Pennsylvania to Chicago?

    Yes. Cheapflights offers flight deals from Pennsylvania to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pennsylvania to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Pennsylvania to Chicago (average of $232). Flying from Pennsylvania to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Pennsylvania to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
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LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Newark to Midway flights
Atlanta to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
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Dulles Intl to O'Hare Intl flights
LaGuardia to Midway flights
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Los Angeles to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Miami to O'Hare Intl flights
Baltimore to Midway flights
Ontario to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Austin to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Hobby to Midway flights
Burbank to O'Hare Intl flights
Orlando to Midway flights
Miami to Midway flights
Portland to O'Hare Intl flights
Dulles Intl to Midway flights
Love Field to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Detroit to O'Hare Intl flights
San Jose to O'Hare Intl flights
LaGuardia to St. Louis flights
Boston to Midway flights

Top 5 airlines flying from Pennsylvania to Chicago

Discover the top 5 airlines that operate flights from Pennsylvania to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$122FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$122Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$135Average$347FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$150Average$270FlexibilityNo cancel feeOn-time63%
DeltaCheapest$155Average$355FlexibilityNo cancel feeOn-timeN/A
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